tert-butyldiphenylsilyl 2-azido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside | 132183-14-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyldiphenylsilyl 2-azido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside
• 英文别名: tert-butyldiphenylsilyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside；(2R,3R,4R,5R,6S)-2-(acetoxymethyl)-5-azido-6-((tert-butyldiphenylsilyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate；[(2R,3R,4R,5R,6S)-3,4-diacetyloxy-5-azido-6-[tert-butyl(diphenyl)silyl]oxyoxan-2-yl]methyl acetate
• CAS: 132183-14-3
• 化学式: C₂₈H₃₅N₃O₈Si
• 分子量: 569.687
• InChiKey: REQJSYJKDHKNCZ-SEFGFODJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  tert-butyldiphenylsilyl 2-azido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 tert-butyldiphenylsilyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  A highly stereoselective synthesis of di- and trimeric sialosyltn epitope: A partial structure of glycophorin A

  摘要：

  DOI：

  10.1016/s0040-4039(00)97201-0
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranose 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以83%的产率得到tert-butyldiphenylsilyl 2-azido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  A highly stereoselective synthesis of di- and trimeric sialosyltn epitope: A partial structure of glycophorin A

  摘要：

  DOI：

  10.1016/s0040-4039(00)97201-0

文献信息

• Synthesis of Tunicaminyluracil Derivatives
  作者：Satoshi Ichikawa、Akira Matsuda

  DOI：10.1081/ncn-120027831

  日期：2004.1.1

  provided the desired cyclized compound 17. In this reaction, the aldol product 13a was also obtained as a consequence of a competitive intramolecular version of DMSO‐oxidation via a 7‐membered ring intermediate. Compound 18 or 19 are ready for use as a glycosyl donor in glycosylations to provide a range of analogues as potential glycosyltransferase inhibitors as well as related natural products. †In honor

  衣霉素核苷类抗生素的关键成分衣胺尿嘧啶衍生物是以二碘化钐 (SmI2) 介导的羟醛反应和分子内普默勒反应为关键步骤合成的。α-苯硫酮 11 是钐烯醇化物的前体，由 d-半乳糖制备。在−40°C 下用 处理 11 导致完全转化为相应的烯醇钐，随后加入尿苷 5'-醛 12 得到所需的羟醛产物 13a、b。通过酮的连续非对映选择性还原和用 mCPBA 氧化，将化合物 13a 转化为亚砜 15。用 Tf2O 活化 15 得到所需的环化化合物 17。在该反应中，醛醇产物 13a 也是通过 7 元环中间体竞争性分子内氧化 DMSO 的结果而获得的。化合物 18 或 19 已准备好用作糖基化中的糖基供体，以提供一系列类似物作为潜在的糖基转移酶抑制剂以及相关的天然产物。†为了纪念和庆祝 Leroy B. Townsend 教授 70 岁生日。#本文构成核苷和核苷酸的第 225 部分：Shuto,
• One-Step TEMPO-Catalyzed and Water-Mediated Stereoselective Conversion of Glycals into 2-Azido-2-deoxysugars with a PIFA–Trimethylsilyl Azide Reagent System
  作者：Ande Chennaiah、Yashwant D. Vankar

  DOI：10.1021/acs.orglett.8b00814

  日期：2018.5.4

  An unprecedented water-mediated and TEMPO-catalyzed, one-step, highly regiospecific and stereoselective functionalization of glycals to 2-azido-2-deoxysugars has been developed using a PIFA-Me3SiN3 reagent system in the presence of Bu4NHSO4 as a phase-transfer catalyst. The method is metal-free, proceeds under mild reaction conditions, and tolerates a variety of protecting groups. Using this method, the synthesis of an important trisaccharide unit bound by the monoclonal anti-I Ma antibody has also been demonstrated.
• Stereoselective total synthesis of glycopeptides bearing the dimeric and trimeric sialosyl-Tn epitope
  作者：Yoshiaki Nakahara、Hiroyuki Iijima、Shohei Shibayama、Tomoya Ogawa

  DOI：10.1016/0008-6215(92)84163-m

  日期：1992.9

  The dimeric and trimeric sialosyl-Tn epitopes, [alpha-D-Neup5Ac-(2----6)-alpha-D-GalpNAc-(1----3)-L-Ser]n-L-Val (n = 2 and 3), which represent part of a clustered carbohydrate region of glycophorin A, a human erythrocyte glycoprotein, have been synthesised stereoselectively. 2-Azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-galactopyranosyl fluoride (GalpNAc unit), Fmoc-L-serine phenacyl ester (Ser unit), and benzyl 5-acetamido-4,7,8,9-tetra-O-benzyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-L - gluco-2-nonulopyranosylonate bromide (Neup5Ac unit) were the key intermediates for stereoselective glycosylation. 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline-promoted elongation of the peptide chain and then hydrogenolysis afforded the title compounds.